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Best of Bootstrapping: Bootstrapping a Virtual Company to $10M from Atlanta

Posted on Friday, Nov 6th 2020

We’re big fans of bootstrapping, virtual companies, and domain knowledge. Field Pros Direct CEO Matt Anderson’s story has all those ingredients.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

Matt Anderson: I’m from a small town northeast of Tennessee called Rogersville. It’s a rural area in the foothills of the Smokies. It’s very beautiful there. I went to East Tennessee State University. I had an aspiration to play football. That’s what drew me to that college. I grew up in that rural town and went on to East Tennessee State. 

Sramana Mitra: What did you do for education? What year did you graduate? What did you do after that?

Matt Anderson: Growing up in a rural area and going to East Tennessee State, it’s hard for me to know what was possible. I wanted to experience something outside of that area. I wanted to go somewhere new. I wanted to go anywhere for the opportunity to get exposed to a bigger city or other types of opportunities that just aren’t available in this rural part of East Tennessee.

I had various job opportunities. One of them was at Crawford & Company. They are the world’s largest independent adjusting firm. They offered a two-week training program where we go to Atlanta and get trained to be an insurance adjuster for a couple of weeks.

Part of the deal was that for the next two or three years, I would go to wherever they would assign me to get exposed to different projects, leaders, and business units. I was a support person that would go all over the country to help with various adjusting projects. That was my first job out of college.

I started in the catastrophe department which dealt with a large volume of claims that could be from a hurricane, hailstorm, or any environmental accidents.  

Sramana Mitra: It would be fire in California and earthquake.

Matt Anderson: Absolutely. It could be environmental accidents like oil spill as well. I was in that department where I would help in various projects, which in a lot of cases would be these catastrophe type of events.

My goal at the company was to one day run that business – a catastrophe profit center. I was there for 10 years. During my last two years there, I was the VP for US and international catastrophe operations for the company. 

Sramana Mitra: What year was this? When did you leave that job?

Matt Anderson: I started in January 2001 and I left in January of 2011. 

Sramana Mitra: What happens next?

Matt Anderson: Towards the end of my career at the company, I had a goal to start my own company. I was thinking of starting something in the adjustment space because that was what I knew so well. I was thinking of a modern version of an adjusting company.

I spent a lot of nights and weekends working on a business plan with the intention of starting my own company. I looked at a lot of franchises. I knew I wanted to own and run my own business.

There was an opportunity with Arrowhead. They were owned by private equity at that time. I was talking to them about them being potentially a customer. Ultimately, they allowed me to start a business to service some of their claims. They were going to be my first client. That’s the biggest fear in starting a new business.

In that particular scenario, I didn’t have any equity. I had a profit share, but they gave me free rein to build this company. We were profitable starting in the third month. I did that for five years. 

Sramana Mitra: Why did they want you to start this company and what were you doing for these clients that they helped you acquire?

Matt Anderson: They were working with another independent adjusting firm that they weren’t happy with for various reasons. They weren’t providing a certain level of service.

I started this company to replace that vendor. Based on the business plan, they gave me a chance and said, “If you are as good as you say you are and this works, then we’ll send you all our claims.” I started with one state and from there kept adding additional states. Their carriers had to approve. It wasn’t a sure thing even when I did that.

I took a much lower salary than what I had at Crawford & Company but in exchange for profit sharing. I didn’t have equity, which I didn’t love at the time. On the flip side, I was nervous about jumping in with two feet and not having a first client and having a long runway. This was a good proving ground for this five-year agreement to see if I could do what I thought I could do. 

Sramana Mitra: Why did you stop doing this? What happened and what was the thinking?

Matt Anderson: Even going into that arrangement I knew that my goal was still to start and run my own company. I ultimately ended up having a five-year agreement. That gave me a date on the horizon on when I wanted to be up and running with a new company. In the background, I started thinking about those things and started saving up for that goal. 

Our conversation continues here.

This segment is a part in the series : Best of Bootstrapping


. Bootstrapping to an Exit
. Why is Bootstrapping Important?
. How Can You Play this Low-Probability Game Intelligently?
. Do NOT Go to VCs as Beggars - Go as Kings
. Excess is NOT Required for Success
. Bootstrap First and Raise Money Later
. Some Bootstrapping to Exit Case Studies
. The Buy Side of Bootstrapping to an Exit
. Blitzscaling vs. Bootstrapping
. Bootstrapping to Unicorns
. Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million
. Mailchimp Bootstraps to $600M Revenue
. Bootstrapping from Arizona to $10 Million
. Bootstrapped Basecamp Executes a No Nonsense Strategy
. How Under30Experiences Bootstrapped to $5 Million
. Bootstrapping with a Paycheck
. How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan
. Seed Investors Who Like Bootstrapped Businesses
. How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million
. Bootstrapping with Services
. How The Intern Group CEO David Lloyd Bootstrapped to $13 Million
. How Passageways CEO Paroon Chadha Bootstrapped from Indiana
. How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million
. Death by Overfunding
. How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+
. How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck
. TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage
. The VC-Entrepreneur Compensation Disbalance
. BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering
. Tremend CEO Marius Hanganu Bootstraps from Romania
. Gesture CEO Jim Alvarez Bootstraps to $10 Million
. SproutLoud CEO Bootstraps to $30 Million from Florida
. Tuft & Needle CEO Bootstraps to Over $100 Million
. Co-founders Bootstrap Linguamatics to Over $10M from the UK
. Ownership Matters
. Vainu Co-founder Mikko Honkanen Bootstraps from Finland
. Entrepreneur Couple Bootstraps to $10M from Colorado
. Power2Motivate CEO Bootstraps to $80M from Canada
. Financial DNA CEO Bootstraps to $10M+ from Australia
. Big Barker CEO Bootstraps a Niche E-commerce Brand
. PrecisionLender CEO Bootstraps to Over $10M from North Carolina
. Master Bootstrappers with Over $1B in Exits
. Ultra Mobile Founder Bootstraps to Over $100 Million
. Bootstrapping a Two-Sided Marketplace to $10M
. Can You Bootstrap a Virtual Company to Over $5 Million?
. Capital Efficient Entrepreneurs Turn $1M into $80M
. Discussing the Journey Through Failure to Success
. From a Small Town to $12 Million
. Bootstrapping to Y Combinator and $10 Million Series A
. Bootstrapping a Marketplace to Over $10 Million
. Freightwise Bootstraps to $33 Million
. Bootstraps First to $5M ARR, Raises $10M Later
. Bootstraps in Europe, Raises Money and Goes Global in the US
. English Major Bootstraps a Tech Company
. Bootstraps with a Paycheck to $15M from Tennessee
. Queue-It Bootstraps from Denmark to the US
. Bootstrapping A Virtual Company To $25M
. ActiveCampaign CEO Bootstraps Using Services to $40M
. Alteryx Bootstrapped with Services to a Public Unicorn
. Inspyrus Bootstraps Using Services to an Awesome Business Model
. CEO Bootstraps Using Services to Millions from Russia
. Wiredrive CEO Bootstraps Using Services to $10M
. Scaling to Over $10M by Bootstrapping Using Services
. Bootstraps Using Services from Poland to a US SaaS Company
. ButcherBox CEO Bootstraps a Perishable Meat Business to Significant Scale
. Waveform CEO Bootstraps to $8M
. Bootstrapped Entrepreneurship from Estonia
. From Laid-off Engineer to Successful Startup CEO
. Imagine Easy Solutions CEO Bootstraps to Exit
. BannerBuzz CEO Bootstraps to $35M
. Bootstrapping a Virtual Company to Scale
. Bootstrapping Using Services from Wisconsin
. Best Tactic for B2B Startups
. Bootstrapping by Piggybacking from Romania
. Bootstrap First, Then Scale with VC Funds
. Bootstrap to +$10M First, Raise Money Later
. Madwire CEO Bootstrapped First, Raised Money Later to $120M
. Bootstrap Using Services First, Raise Money Later
. Wonderful Bootstrap with a Paycheck Story
. RushOrderTees CEO Bootstraps to $23M
. Bootstrapping with Freemium and Free Trials to $13M
. Bootstrapping, Pivoting, Gaining Liquidity, Scaling to $100M+
. Bootstrapping with Affiliate Marketing
. Bootstrap to Exit, Bootstrap Again, Then Raise VC Money
. Bootstrapping Using Services to $12M
. Bootstrapping an Ad Tech Company from Paris
. Bootstrapping a 100% Virtual Company from Ireland
. MiQ CEO Bootstraps with Services from London
. Bootstrapping to $8M During the Covid Crisis
. Bootstrapping a Marketplace from Brazil
. Bootstrapping Using Services from Sweden
. What Should Startups Do To Raise Seed Capital in 2021?
. EdTech Unicorn Bootstrapped First from Canada
. Coalition Technologies Co-founders Bootstrap to $10M
. Bootstrapping a Virtual Company to $10M from Atlanta
. Bootstrapping a SaaS Company with a Paycheck and Scaling
. Bootstrapping with Services to $20 Million
. Onit CEO Bootstraps First, Raises Money Later
. Pura Vida Founders Bootstrap to $130M
. Lawline CEO Bootstraps to $10M
. Bootstrapping a Technology Product Company from India
. Codesigned CEO Bootstraps Using Services
. Rukkus CEO Follows Bootstrap First, Raise Money Later Strategy
. Bootstrapping and Managing a Successful Pivot
. Ukrainian Entrepreneur Bootstraps to Global Scale
. Bootstrapping a Niche E-Commerce Venture
. Bootstrapping Planon to $100M from The Netherlands
. Co-founder Bootstrapped with a Paycheck from Indiana
. Bootstrapping an Education Company
. Bootstrapping an IoT Company from North Carolina
. Serial Bootstrapper Bootstraps to $27M
. Bootstrapping Identity Automation Using Services from Houston
. Bootstrapping ProjectManager.com from NZ, Scaling in the US
. Bootstrapping to $15M in Three Years
. Peruvian Entrepreneur Bootstraps to $200M
. JotForm Founder Bootstrapped with a Paycheck
. WeGoLook was Bootstrapped from Oklahoma
. Bootstrapping AutoClaims Direct to $15M
. Meltwater Founder Bootstrapped to $200M
. Bootstrapping to $20M From London
. Synechron CEO Bootstrapped to $300M
. Unique Vintage was Bootstrapped with a Paycheck
. Toptal CEO Bootstraps a Virtual Company to Scale
. Bootstrapping to $45M from Chicago
. Vacasa Co-founder Bootstrapped to $100M
. Bootstrapping Infinitely Virtual All The Way
. Bootstrapping to Exit Discussion with David Lambert, Right Side Capital Management
. Bootstrapping a Healthcare IT Company to $100M
. Discussing Seed Rounds with Cindy Padnos, Illuminate Ventures
. Auction.com Bootstrapped to $180M in Online Real Estate
. Discussing the Silicon Valley – India Corridor with Naren Gupta of Nexus Venture Partners
. Bootstrapped with a Paycheck to Techstars and Acquisition
. Discussing People vs. Market with Jon Staenberg, Staenberg Venture Partners
. Bootstrapping a Highly Profitable Company in Social Media Marketing
. Discussing Investments in Indian Startups with Anand Daniel, Accel Partners
. Bootstrapping an Evergreen Business from Oregon
. Discussing Startups in Africa with Osayi Igharo, Ripple VC
. Investing in Concept Stage Startups with Matt Holleran, Cloud Apps Capital Partners
. Serial Entrepreneur Bootstrapped Two Startups to Huge Revenue
. Discussing Investment Strategy With Deepak Jeevankumar, Dell Technologies Capital
. Bootstrapping Hotelplanner.com to $20M with Intelligent Financial Engineering
. Discussing Investing Across Sectors in India with Swapna Gupta, Qualcomm Ventures
. Bootstrapping Cleverbridge From Germany
. Discussing Open Opportunities with Hemant Mohapatra, Lightspeed Venture Partners
. Bootstrapping E-commerce Company Fun.com
. Discussing Seed Rounds with Bruce Cleveland, Wildcat Venture Partners
. From Friends and Family Funding to $30M Exit
. Discussing the Evolution of the Indian Startup Industry with Sasha Mirchandani, Kae Capital
. Lean Company Bootstraps to $7M
. Saatva Co-founder Bootstrapped a $25M E-Commerce Company
. Looking at Terms with Heidi Roizen of Threshold Ventures
. ADDA Co-founder CEO Bootstrapped with a Paycheck in India
. Duda Co-founders Bootstrap with Paychecks
. The Importance of Building Value with Shomit Ghose, Onset Ventures
. Get Real Health Founder Bootstrapped Using Services
. Bootstrapping Unique Vintage Using a Paycheck
. Discussing E-commerce Startup Trends with Daniel Gulati, Forecast Fund
. Bootstrapping a Digital Startup with a Paycheck
. Discussing Seed Stages with Amir Banifatemi of K5 Ventures
. Bootstrapping Avelead Using Services from Atlanta

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